On the Hunt: Holiday Shopping in Old Town Winchester

On a blustery Thursday, The Valley Today host Janet Michael and Brady Cloven, Executive Director of Friends of Old Town, set out on a spirited adventure through Winchester's historic walking mall. Their mission? To uncover the best last-minute holiday gifts while showcasing the vibrant local businesses that make Old Town a shopping destination. Despite the biting wind, their enthusiasm never wavers as they pop into shops, chat with owners, and gather a sleigh-full of unique gift ideas. A Shop-by-Shop Gift Guide Their first stop, Back to the Media, offers a nostalgic twist on holiday shopping. Mari recommends pre-loved gaming consoles, a treasure trove of vinyl records, and quirky imported snacks—think garlic shrimp Doritos and stuffed-crust pizza chips—for stocking stuffers that spark conversation. Next, at Wilkins Shoe Center, Kendra highlights the perennial popularity of gifting shoes, from Uggs to Birkenstocks, and reminds listeners that a gift certificate is always the perfect fit. The warmth of the store contrasts with the chilly weather outside, making it a cozy haven for holiday shoppers. At Incredible Flying Objects, Drew and Anna introduce a playful selection of gifts, including collectible Sonny Angels, buildable Blokees toys, and novelty sodas and candy canes with flavors as wild as chicken soup and salmon. The store's pinball machines add a dash of retro fun, inviting families to linger and play. Handmade Artistry and Local Flavor The journey continues at Tin Top Art and Handmade, where Jen showcases an eclectic mix of candles, soaps, ornaments, and pottery—all crafted by local artists. Brady raves about the shop's unique t-shirts and postcards, while Janet marvels at the rotating gallery of one-of-a-kind art pieces. The message was clear: if you see something you love, grab it before it's gone. No tour of Old Town would be complete without a stop at the iconic Snow White Grill. Danny Turner, the ever-enthusiastic proprietor, offers up vintage toy cars, branded hats and shirts, and, of course, the legendary cheeseburgers. Gift certificates, he notes, are a delicious way to spread holiday cheer all year long. Personal Picks and Community Spirit Janet shares personal favorites like Winchester Book Gallery, Polka Dot Pot, and Nibblins cooking classes, as well as experiences like tickets to Bright Box shows and craft brewery visits. Art lovers are encouraged to explore the many galleries and artist co-ops sprinkled throughout downtown. At Abija Blue, Susan dazzles with handmade alpaca blankets, shawls, and dog ponchos, along with Turkish towels, jewelry, and whimsical finger puppets. The shop's global selection ensures that every shopper can find something special, regardless of budget. The Power of Shopping Local Throughout their stroll, Janet and Brady emphasize the importance of supporting small businesses, especially during the critical holiday season. They highlight the Old Town Holiday Gift Guide—a comprehensive directory and map available both in print and online—as an invaluable resource for navigating the diverse offerings downtown. Gift cards, they suggest, are not only thoughtful presents but also a lifeline for local shops during the slower winter months. Wrapping Up with Warmth As their conversation draws to a close at Hideaway Cafe, Janet and Brady reflect on the joy of discovering new favorites and the satisfaction of giving back to the community. Their lively banter and genuine appreciation for Old Town's merchants capture the spirit of the season: connection, generosity, and the magic of shopping local.